Pokemon: Dating Confusion
by RedHoodLover
Summary: When Ash travels home to Pallet Town to take a break from his travels, he is greeted by both enemies and friends from his past. What happens if May falls for Cilan? Or if Iris gets chased down by Brock? If Dawn and Tracey start hanging out? Or, worst of all, Misty dates Gary! How is everyone going to react?
1. Chapter 1

** Okay, this is going to be my first multi-chapter story. I'm actually really excited about this, so let's just get right to it. Please review though!**

Pokemon: Dating Confusion

Chapter One: Of Friends and Foes

"Wow, it's been awhile since I've been home." Ash said, walking along the road to Pallet Town. His signature backpack was slung over his shoulders, and his Pikachu was sitting on the back of neck, his feet on the backpack to balance himself.

"Yeah, you've been traveling with us for quite some time." Cilan agrees, nodding his head.

"I wonder what Pallet looks like…" Iris muses, almost to herself if her Axew hadn't been listening from his perch in her hair.

Ash smiles, clearly excited about going back.

"I'm going to be staying home longer this time. Normally I would want to rush to the next region, but I think Pikachu and me need a small break." Ash admits, knowing his Pokemon craved ketchup, and his mother always seemed to have an endless supply.

Iris opened her mouth to speak, but was interrupted, as a sudden yell was heard. She turned her head, and was surprised to see Ash gone.

"I see Pallet Town!" Ash called, running slightly off the course of the trail in his eagerness to get back.

Iris rolled her eyes, then nodded to her Axew, signaling for him to hold on. She burst into a sudden run, taking off after Ash. Cilan half smiled, then briskly ran after them, at quite a slower pace.

Ash didn't even look back, concentrating on other things.

_ It's going to be awesome to see Professor Oak again. I'm looking forward to seeing Tracey as well. My mom will like having me home too…_

He thought, too deep in his thoughts to be paying any attention to where he was running. He paid enough attention later, **after **he hit the front door of his house.

A loud bang was heard, and Mrs. Ketchum walks to the front door, opening it.

"Hello and who is-" She stopped, looking down and seeing her son.

"Ash?"

Ash fell forward as the door opened, at his mom's feet. He stands up weakly, rubbing his nose.

"Ow, and hey, why's it so dark in here?" He asks, stepping into the doorway of his house. As he looks around, he realizes his mother is gone.

"Mom?" Ash asked, at this point getting suspicious. He walks into a hallway and puts his hand on the knob of the kitchen door, turning it slowly.

"Pika pi." Pikachu whispers.

'This could be a trap.' Is what Pikachu means.

Ash, nods slightly, understanding a few simple phrases in Pikachu language at this point.

"Probably Team Rocket…" He mutters, then shoves the door open quickly, barging in. Ash sees several figures in the dark, so he tackles the closest one and shouts,

"Take that Tea-"

"Happy birthday Ash!" A chorus of voices say. The lights flicker on, and Ash blinks, getting used to the sudden brightness. Looking down, he sees he tackles a lifesize blowout of himself. He would've been embarrassed, but he suddenly spied a cake in the corner of the room, sitting on the kitchen counter. He zooms over to it, eyes gazing at it longingly.

"Ash! No cake until after the party. And remember to thank the lovely girls who planned this party." His mother says, nodding to the four girls standing beside her.

"Misty? May? Dawn? What are you guys doing here?" Ash asked, momentarily forgetting the cake as he rushed over to greet them.

"Well, your mom said she was planning a surprise party for you, so I decided to take a break from my gym to visit." Misty explained.

"I missed seeing you guys, and wanted to hang out again." May replied, winking at everyone.

"I heard the words party, and knew everyone would be here! I was planning the balloons, the streamers, setting up the guest list…" Dawn said, counting the things off on her fingers.

Ash nods, understanding those reasons. His gaze suddenly shifts to the left, and he spots Iris.

"How did you get here before me?" He asked, tilting his head in confusion.

Iris merely rolled her eyes, sighing.

"Really Ash? You know there's a back door, right?" She said, shaking her head.

Ash glared back, opening his mouth to argue when Dawn stopped them.

"Hey guys! Look, the other guests are here!" She exclaimed, shoving past them and opening the front door.

The others glanced at each other, their eyes mirroring their confusion.

"What other guests?" They all said simultaneously.

As they spoke, the guests entered. The first was of course Cilan, who had decided not to burst through the back door unannounced. The second, was the gym leader of Pewter City. Brock, one of Ash's oldest traveling companions, stepped inside.

He and Cilan were already engaged in a conversation about Pokemon, mostly pertaining to Pokemon food. They didn't notice the others, to engulfed in the topic. Cilan and Brock walked over to the counter, standing and continuing to talk.

"Hi everyone!" Tracey said, being the third person to enter the room. He immediately ran over to the girls, proceeding to sketch them.

While Misty was mostly unaffected by this, the others were quite affected. May decided to ignore him, trying to follow Misty's example.

"Uh, what are you doing?" Iris asked uncomfortably. Dawn, however, decided to embrace it.

"Hi! Are you drawing us? Come on girls, strike a pose!" Dawn said, gesturing at them to do so.

They all shook their heads, snickering a bit. Tracey continued to draw, appreciating that Dawn was trying to help.

"Thanks a ton for helping Dawn! I normally sketch Pokemon but the professor said I should be well rounded!" Tracey said, his pencil never stopping.

"Gee thanks!" Dawn said, sending him a wink.

"You're a natural at this Dawn!" Tracey complimented.

"You think so?" She asked hopefully.

_ You hear that Dawn! He says you're a natural! You could be a model someday…_

Dawn smiles dreamily, thinking to herself.

Trip walks in, sighing. Beside him is Gary, and both aren't exactly excited at the prospect of coming to a party for their rival. But on the other hand, knowing your enemy is a good strategy for fights, with or without Pokemon. (Plus Mrs. Ketchum is very persuasive.)

"Trip, Gary!" Ash exclaims, surprised to see them there.

"Uh, mom, what are they doing here?" Ash asks, leaning in to whisper in his mom's ear.

"They're nice boys, and you know them. Now you better be polite to them!" His mom whispers back.

Ash sighs resignedly, slumping against the kitchen wall. It had been a strange beginning to a day. First of all, he had forgotten his own birthday. How he had managed to do that he didn't know. Then he was greeted by two of his rivals, the oldest and the newest.

_ Oh well, they're not __**so **__bad. Maybe we can get along-_

"Hey Ash! Still have that scrawny Pikachu I see." Gary said, interrupting Ash's thoughts.

Ash sighed, glaring and turning around to face him. Pikachu glared too, some electrical sparks appearing around his whiskers.

"And what's that supposed to mean?!" He snaps.

_ Just when I think we might get along…_

Ash adds in his brain.

Gary just smirks, chuckling a bit. He doesn't say anything, putting his hands in his pockets and walking over to the girls.

"He's right you know. That pathetic Pokemon can't stand the tough competition." Trip agrees, having heard the conversation.

Ash starts to hit boiling point, but thankfully May had glanced over and seen the fight.

"Hey boys! Look, Mr. Mime is dancing!" She says, pointing at the Pokemon, which, strangely enough, dances while it dusts furniture.

This causes a small distraction from the argument, long enough for Trip to decide that arguing with someone like Ash was a waste of time. He walks to a corner of the room, glancing around in boredom.

May sighs, looking relieved. She smiled, stepping away from the other girls and walking over to Brock and Cilan. She tilts her head at Cilan curiously, her hair falling out of its bandana.

_ He reminds me of someone…_

She thinks, closing her eyes as she concentrates. Unfortunately, watching where you were going while walking was very necessary.

"Wah!" She cries out suddenly, tripping over a bag of groceries. She flails her arms, trying to catch herself. Suddenly, she feels someone stop her from falling, and she opens her eyes again.

"Huh?" She says as they turn her around to face them.

"That was quite a fall. Luckily I caught you, or you might have gotten hurt." Cilan says, smiling at her kindly.

She blushes slightly, but doesn't have a chance to say anything. He sets her down gently, but his arms are still around her waist.

"I, um, I think I'm fine now…" She says, still blushing.

Cilan nods, setting her down beside him in a chair, and he and Brock proceed with their discussion. Several times May had to consciously tell herself to quit staring at Cilan.

_ What is up with me? I know he reminds me of somebody I know…_

Gary, standing near Misty and parallel to Iris, smirked slightly.

"Isn't that May? Looks like someone has a new crush." He mutters quietly, mostly to himself, but Misty is close enough to hear it.

"Yeah, sure Gary." Misty said, attempting to roll her eyes but decided not to. She looked up at him, getting a better look.

_ Wow, he's gotten taller, and more muscular too…_

She thinks to herself, eyes widening slightly.

"Take a picture, it lasts longer." Gary said, snapping Misty out of her thoughts.

She involuntarily blushed; she hadn't meant to stare at him.

"Like I would take a picture of you." She says, trying to regain her composure.

"You would like to? Alright then." He winks at her, flashing a grin.

Misty blushed again, giggling slightly.

_ What am I doing? Am I flirting with __**Gary**__?!_

She gulps, but doesn't show her discomfort.

Gary gives her another grin, yawning.

"You bored too?" He asks her.

"Kinda hard to be around you." She replies. It wasn't until the words were out of her mouth that she realized it _did _sound like she was flirting. She had meant it sarcastically, but that wasn't how Gary interpreted it.

"Yeah, I'm special like that." He laughs, not a mocking laugh, but an actual laugh.

Misty laughs back, and realizes she never really got to know Gary. He was always just, 'Ash's rival'. She smiled at him, a genuine smile.

"Don't get cocky." Misty said, enjoying flirting-but-not-flirting with him.

"Oh I won't. Not when you're around anyway." Gary said, his eyes twinkling.

"I don't think you want to eat here. Mr. Mime's cooking is terrible. Want to go get a burger?" He asked casually.

Just as he speaks, an exploding noise is heard from the other end of the room. Everyone turns around and see Mr. Mime standing near an oven of burnt cookies.

Misty sighs, thinking hard.

_ Gary just asked me out! What do I do?!_

Looking back at Mr. Mime, she shrugs, deciding one unofficial date wouldn't hurt.

"Sure, okay. Let's go then." She said.

Gary nodded, the look of victory clear in his eyes. He walked up to the door, opening it and leading her out.

Ash, having been distracted by the dancing Mr. Mime and then the explosion, happened to look over at them as Misty was about to step outside with Gary.

_ Where is she going with him?_

He wonders, unable to stop the jealous feeling brewing inside. He was too late to do anything though, seeing as the door was being closed at that very moment. He sighs, then turns around, marching up to Mr. Mime and his mom, seeing if he could get one of the slightly less burnt cookies.

Brock nodded, having talked to Cilan for a while he looked at the clock. Knowing there was plenty of time before the party started, he stood up, smiling at May and Cilan.

"I think I'll go check on everyone else." He said, stepping away when he saw Iris.

"Hey, I haven't seen her before." He said, then he snapped into lovesick Brock.

"Hey beautiful! Want my number, my email address, the keys to my gym?" He said quickly, having rushed right beside her.

Iris jumped, a bit surprised.

"What? Who're you?!" She asks, very surprised.

"Your knight in shining armor!" He answers, his heart eyes popping out.

Her eye twitches, and she backs away.

_ This must be Brock…_

She thinks, then snaps her fingers.

"Look, it's Nurse Joy!" She shouts, pointing behind him.

He turns around anxiously, looking for her hopefully.

"Nurse Joy?! Where?" He asks, eyes scanning around the room.

Iris, feeling relieved, uses this moment to escape. She runs to a corner of the room, a darker corner where she hopes that Brock couldn't see. Luckily she was in a different corner than Trip, or that might have caused some trouble. She spies Tracey, still sketching Dawn.

Tracey pauses to rest his hand for a minute.

"I might take a break and continue this later. I've already done the main parts anyway, and I can color it tomorrow." He tells Dawn.

She nods, relaxing and stretching her arms out.

"That was fun! We should hang out again sometime!" She said, smiling.

"Yeah, you're amazing to sketch! And I would love to draw your Piplup sometime." Tracey replied as he put away his pencils and sketchbook.

"That would be awesome!" She answered, petting her Piplup's head softly.

"That's good! I'll see you outside the Professor's lab tomorrow?" He offered.

Dawn nodded, jumping up happily.

_ This is so cool! I really might be a model._

She thinks to herself, then winks and walks toward Ash, his mom, and Mr. Mime.

May sat in silence. When Brock had left Cilan had pulled out a notebook, and once he started to write things down he didn't stop. She sighed, pushing back a loose strand of hair.

Cilan looked up, hearing a sound. He realized May had been sitting there that whole time, so he mentally smacked himself for being so rude. He quickly put away his notebook, and looked at her.

"I'm sorry if it seemed like I was ignoring you May. You see, I was just writing down some notes. Brock sure does know quite a lot about Pokemon." He said with a charming smile.

May smiled back up at him, glad for the conversation.

"No it's okay! It's fine to be busy." She replied.

"Not when there's a charming young lady sitting beside you it isn't." Cilan answered.

She blushed, her cheeks reddening.

_ Charming young lady? _

She thought, blushing a bit more.

"I, think I'm going to go get something to ea-" She trips as she tries to stand up, and ends up falling onto Cilan's lap.

_ Great job May. Could this get any worse?  
_She moans quietly, trying to hide her face.

At that very moment, the door creaks open, and a young male coordinator walks in.

"May?"

** Dun dun dun! I'm pretty sure you all know who just came in. As if that wasn't enough, he isn't the last guest! Stay tuned for more, but reviews make me work faster! Also, if you have any questions feel free to ask! Any suggestions will be considered of course. Thanks so much for reading!**


	2. Chapter 2

** OMG! 4 favorites, 3 follows, and 3 reviews? That's hard to come by in the Pokemon category. Thank you guys so much! Please, keep reviewing! They make me write faster!**

Pokemon: Dating Confusion

Chapter Two: Another Guest

Misty picked up her burger, nibbling a small piece off of it. She gave Gary a dubious glance as he picked up a huge bacon wrapped burger, preparing to take a bite.

"How can you eat that?" She asked, nose wrinkling slightly.

He shrugs, grinning mischievously back at her.

"Like this Misty." He replied, taking a large mouthful of the sandwich.

Misty rolls her eyes indignantly.

"That's very repulsive Gary Oak." She informs him, her lady-like side feeling utterly disgusted.

"How else are you supposed to eat this?" He jokingly protests, holding the huge burger out for her to look at.

She gives him a look, with a competitive gleam in her eye.

"Is that a challenge Gary?" Misty replied, tossing her red hair to the side of her face.

"So, I'm guessing you accept the challenge?" He answered, leaning forward to look her in the eye.

They both stared at each other, almost as if they were waiting for the other to back down. Misty gazed into Gary's eyes intently, determination written all over her face. He wasn't affected by her look, so he merely chuckled.

"I guess that's a yes. Waiter, another Bacon Wrapped Onion Burger Special, please." He said, waving his hand toward a waiter. The man immediately rushed into the back of the restaurant, quickly coming back out and bringing on a silver, gleaming tray the large sandwich. He placed it on the middle of the table, walking to another table swiftly.

Misty eyed the sandwich, almost scrutinizingly. Her brow furrowed as she concentrated, holding up the top of the bun to better examine the insides. She bit her lip, frowning.

"Mine is bigger than yours." She said at last, placing the top bun back on the sandwich carefully.

Gary opened his mouth, ready to protest.

"How so? You're too small of a girl to eat that whole thing anyway…" He shrugged, not quite believing in his own statement but it was too late to back out now.

Her eyes flashed, and if she had been a superhero she would've had laser vision. The heated stare got Gary's attention, as she could tell by the way he shifted slightly in his seat.

"Bring it, Wanna-Be Pokemon Master." She smiled, with an air of satisfaction as she knew that would get to him.

He sent her a glare, trying to stay light-hearted but also knowing she had crossed the line.

"Let's go, Mermaid Girl." He gave her one more look before starting in on his burger.

Misty, who had been thinking of a good comeback, saw him scarfing down half his sandwich already, so she frantically made a grab for her own sandwich, taking bigger bites than were probably safe.

Gary glanced over, but as soon as he noticed his gigantic lead, he slowed down a bit, almost mocking her as he ate extremely slowly, indicating it was easy to beat her by the fact he could beat her eating at a snail's pace.

Misty shot him a fierce glare, taking another bite. She opened her mouth to say something, but as she was forming the words, the food got lodged in her throat. Her face immediately turned red as she gasped for air. She couldn't talk or breathe, so she banged her fists on the table, trying to get Gary's attention.

He looked up, his mouth forming an O once he saw she was choking. He practically jumped out of his seat, scrambling to reach her. His leg was caught in the foot of his chair, so he tripped, landing with a crash beside the choking Misty. Grabbing onto the table, he stood up, carefully untangling his leg from the wooden seat. He reached out his arm, taking her hand and pulling her up from the seat. Gary stood her up at the proper angle, then wrapped his arms around her waist and performed the Heimlech Maneuver.

Misty felt a slight thumping on her stomach. As it continued, she noticed the lodged bit of food was loosening. Her passageways started to open, and the food shot out, hitting an older man in the back of the head.

Gary sighed in relief, sitting back in his own chair across from her. He smiled, happy that she was okay. His smile turned into a frown as he noticed Misty pointing to a man, walking toward them quite briskly.

Gary could barely stop from laughing after he realized it was Professor Oak, covered with a small spray of food on his head.

"Hey Gramps, what's up?" He said, trying hard not to snicker.

Misty looked embarrassed, so she tried to help things out as the professor looked like he would explode.

"It was an accident, I was choking on my food, and Gary used the Heimlech Maneuver, which made me cough out the food. We weren't trying to hit you…" Even Misty struggled to keep the giggles at bay. The professor's face relaxed, after noticing Misty was also there.

"Ah, well, I suppose it couldn't be helped. What are you two doing here anyway?" He asked, creasing his forehead in thought.

Misty was about to tell him that Gary had taken her out to dinner when she thought better of it.

_ That makes it sound like a date…_

She thought, then sighed. A waiter came over at that very moment, handing Gary the bill.

Gary took out his wallet, leaving the money for the food and a good-sized tip too. He set it down on the wooden table, walking over to where Misty and Professor Oak were standing.

"I'll probably head home. See you later Misty." Gary said, saluting them and walking away toward the his grandfather's lab.

Misty felt a small smile appear on her face, and she picked her arm up and waved.

"Bye Gary!" She called, loud enough for him to hear.

Gary didn't turn around, but a smile was on his own face as he walked away.

"Where are you staying tonight Misty?" Professor Oak asked the young girl.

"I think at Ash's house. His mom said we could spend a night or two." She explained to him.

"Ah. Would you like a ride?" He asked, gesturing to his car.

She nodded, walking past him to the vehicle. She waited, watching as he strode behind her and unlocked the passenger seat.

"Hop in," He said, to which she obeyed speedily.

He shut the door of the convertible, opening the one on the other side and climbing in. After they had both gotten settled, he cranked the engine, starting up his car. They traveled a few minutes in silence, when the professor decided to ask Misty a question.

"Why were you on a date with my grandson?"

Misty groaned, putting her face in her hands.

_ This is going to be a fun drive home._

[At Ash's House]

May gulped, squeezing her eyes tightly shut, hoping the voice didn't belong to whom she thought.

_ Please not him. _Anyone_ but him._

She silently pleaded, though inside she knew it had to be him. Cautiously she glanced up, and was met with a rose in the face.

"Here, this one actually is for you." Drew said, handing it to her.

She blushed, practically springing off Cilan's lap and standing up next to Drew.

"T-thanks…" She managed to say, laughing nervously as she accepted the beautiful rose.

"Don't mention it. Consider it a congratulatory gift for finally getting a boyfriend." Drew laughed, though it was almost a forced one as he gestured to Cilan.

May's face went beet red, partially from embarrassment and also from anger. She gripped the rose tightly as she stood on her tip toes so she was taller than him.

"Now you listen a minute! He is _not _my boyfriend, and you are an arrogant jerk!" She snapped, getting right up in his face.

He almost sweat dropped, but caught himself just in time. Drew chuckled, pretending to be amused. He ignored the fuming May and walked past her, heading toward the other side of the kitchen where Ash and Dawn were.

"Drew! You come back here! I wasn't finished with you!' May said angrily, shaking her fists. She scowled, her brow furrowing in rage as she stomped the opposite direction, ultimately toward the door.

Drew was leaning against the wall of the kitchen, eyeing the cookies with suspicion. He didn't dare eat one of those nasty, burnt things. He sighed quietly, leaning his head back.

Dawn and Ash had watched the scene with curiosity, but decided not to get involved, personally being afraid of what would happen if they interfered.

"Hm, hey Piplup, do you want to go outside and train?" Dawn asked her Pokemon, smiling cheerfully.

The Piplup had nodded, so Dawn, looking happy, raced outside to train. The girl wasn't paying attention to the fact that Drew had also been heading toward the door to train and blow off some steam. So, cramming into him, they both tumbled toward the floor.

Luckily, May had been right there so she helped them up.

"Oh, are you okay?" She asked with concern.

Drew sat up, wincing as he rubbed his head.

"Yeah, I think I'm-"

"Not you! I meant Dawn." She said, sending him an eye roll as she helped Dawn to her feet.

Drew narrowed his eyes, about to stand when the door opened, knocking him back down.

"Paul?!" Came a chorus of voices around the room.

Paul looked around the room, surveying it carefully. He stepped over Drew, who was sprawled out on the floor.

Everyone watched him, looking astonished. Even Mrs. Ketchum was surprised he actually showed up.

As Paul glared back, they quickly looked away, pretending not to notice him.

He took a seat at the table next to Cilan and Brock, who had recently sat back down after being unable to find Iris.

May had helped Dawn to the buffet table with the half burnt cookies, and they were both chatting with each other, ignoring Drew, who had by this point stood up, and was brushing himself off near the door.

"Thanks for the help." He mutters sarcastically. No sooner had he said that than the door had opened, knocking him to the floor, again.

"Hey guys, I'm ba-" Misty stopped, looking down and seeing Drew.

"Is he okay?" She asked, looking confused and concerned.

They all shrugged, then went back to their chatting. Misty, after giving him a glance and feeling sure he was okay, stepped around him, walking over to Dawn and May.

Mrs. Ketchum suddenly walked into the middle of the room, clearing her throat. Everyone turned their heads to look at her, giving her their full attention.

"Well, I'm afraid I don't have enough space for everyone," She begins, "so Cilan and Brock, you, along with Tracey and Gary of course, will be staying at Professor Oak's tonight. I've already called and they're expecting you in a few minutes."

Cilan and Brock glanced at each other, then shrugged, standing up. They gathered up their bags, then made their way to the door, opening it and stepping out into the cold night air. It was 8 at night, so most of them would be heading to sleep soon.

"Alright, now with the rest of the sleeping arrangements. Ash and Drew, you'll be sleeping in Ash's room. There's a mattress on the floor for you Drew. Trip and Paul, you two will be sharing the guest room." Once she finished, everyone looked at their roommate.

Drew and Ash both looked like they didn't really care, but Paul and Trip were glaring daggers into each other, practically screaming, "You expect me to room with _this _guy?"

As Ash, Drew, Paul, and Trip walked to their respective sleeping quarters for the night, Dawn tilted her head, some blue bangs slipping out from beneath her hat.

"Where are we going to sleep?" She asked.

Mrs. Ketchum smacked her own forehead, clearly having forgotten something.

"Oh, yes. Hehe, I forgot…" She admits, then waves her hand at them to follow her.

She leads them past a hallway, it being filled with pictures of Ash and his friends. They would occasionally stop to admire the pictures, often reminiscing about their old adventures.

"We're here!" Mrs. Ketchum said, opening a door and walking down a flight of stairs. They quietly creaked, and reaching the bottom she opened another door, letting them look inside.

It had pale, rosy pink walls. There was plain white carpet on the floor, still fuzzing up as if it were new. A TV sat near one wall, and there was a huge brown couch parallel to it. They gasped, impressed.

"Wow, this place is awesome!" Dawn said, immediately jumping onto the sofa, wrapping up with a blanket she found on it.

May was about to do the same, but spied a mini fridge in the corner. Feeling her stomach rumble, she grinned, practically dancing over to it.

Misty turned to Mrs. Ketchum, smiling with gratitude.

"You sure have a nice den room." She said.

"Thank you! And if you're wondering why the walls are pink, it's because Ash used to come in here all the time when he was little. He wouldn't do anything else but watch TV. But then I painted the walls pink, got new carpet, and suddenly he never steps foot in here…" She said, smiling back at the young red head.

Misty laughed, shaking her head as she went to join her friends.

Suddenly Mrs. Ketchum smacked her forehead again.

"I forgot Iris!" She exclaimed, rushing out of the room.

The girls looked at each other, then shrugged, giggling to themselves.

May suddenly squealed, turning her head around so fast that her head looked like a red and brown blur.

"Guys, did you know there's ice cream sandwiches in here?" She asked excitedly.

Misty smirked, running over and peeking through the fridge.

"Hey, I call the lime soda!" She said, snatching a bottle of it.

May glanced at the food again.

"I call the strawberry soda then!" She said, taking a different bottle, looking pleased as she and Misty went to sit down beside Dawn on the couch.

Dawn had already sprung up, and was at the fridge in an instant. After a few minutes of searching, she held something up, beaming happily.

"Look, I found an orange soda!" She said, holding it up as if it was a trophy.

The other girls sighed, almost wishing they had found it first. As Dawn skipped back over to the them, Iris stepped in, looking around the room.

"Wow," She said, unsure if it was creepy for a den room to have pink walls or impressive.

She sat down on the floor, in front of the couch where the others were sitting.

"Mrs. Ketchum went to bed for the night." She informed them, yawning slightly herself.

Misty nodded, then suddenly grinned, looking at them deviously.

"I have an idea! Who wants to play 'Truth or Dare'?" She asked.

Iris perked up, smiling competitively.

"Count me in!" She exclaimed.

Dawn looked at May, who in turn shrugged.

"Sure," Dawn said just as May said, "Why not?"

Misty nodded, almost seriously.

"Alright, this is a free for all. This means we don't have to go in a circle, and we can ask whoever we want. No inappropriate stuff for dares or questions though." Misty told them, then looked at May.

"Truth or dare?" She asked.

"Um, truth." May replied, a bit wary of her dares.

"Okay, do you have a crush on Cilan?" The older girl asked May with an evil grin.

May blushed, starting to stutter.

"Er, um, well… m-maybe a little…" She admits in a low tone, and the girls could barely hear her answer.

"Alright, who wants to go next?" Misty asked.

"Misty, truth or dare!" May said before anyone else could answer.

Misty frowned in thought, then shrugged.

"Dare."

**What will May dare Misty to do? Review and find out! (Seriously, reviewing does make me work a lot faster.)**


	3. Chapter 3

**Hey hey hey! I'm back, and here's the next chapter! Thank you guys so much for all the support, and here it is! Please, R and R! It really does improve my writing speed.**

Pokemon: Dating Confusion

Chapter Three: A Truth and a Dare

May thought for a moment, scrunching her eyebrows in deep thought. She tapped her chin, almost as if thinking that would speed up the thinking process.

"I dare you to sneak into Ash's room and steal something from it!" She said finally, crossing her arms with satisfaction.

Misty, who would have normally protested against something like that, had been taken control of by the game. It would inspire people to do things they normally wouldn't, and, though not everyone was affected by it, she was one of those who was. You could tell by her fiery temper, the competitive gleam in her eye. A dare, it was hard to back out of.

So, standing up immediately, she slipped quietly out of the room, creeping quietly along the hallways, searching for Ash's room. She thought she remembered that his was the, third door to the right? The second door to the left? She sighed, shaking her head. This could take awhile.

Ash shifted slightly, sitting on top of his bed with Pikachu, who insisted upon eating a bottle of ketchup before bed every night. He sighed, looking over at Drew, who was studying Ash's wall of Pokemon badges.

"So, you won all of these?" Drew asked, turning around to look at Ash.

He nodded, his raven-black hair bobbing up and down with his head.

"Yeah, these are from Kanto, the Orange Islands, Johto…" Ash continued, going through every region he had been through.

"Not bad, I guess. Do you have anything to do in here?" He asked, looking extremely bored.

Ash thought for a moment, then dipped beneath his bed, reaching his arm around underneath it frantically, as if searching for something. He could feel his fingers touch something, so he stretched his arm as much as he could, and grabbed a corner of it. Pulling it out in triumph, he showed it to Drew.

"I got this when I was younger. A tape recorder. You can record anything on it." Ash said, proudly sporting it off.

Drew frowned, shrugging as he gazed at it.

It had a microphone connected to one end, and a few buttons on the top. The controls seemed simple: play, rewind, stop, and record. Drew reached a hand out, taking the old looking toy. Getting a closer look her realized it was made years ago; Ash must've gotten it when he was three years old.

"Are you sure this thing still works?" Drew asked doubtfully.

"Of course it does!" Ash said, snatching it back from him and clutching it to his chest.

The old toy had sentimental value; seeing how it was one of his earliest toys. Out of the ones he remembered anyway.

Drew gazed at it for another moment before hearing something outside the door. Tilting his head slightly to the left, he could hear a shuffling noise, a sign that someone was outside the door. Turning to Ash, he smirked, then motioned for him to follow. They both stood up, and Drew put a hand to the knob of the door. He turned it quickly, and they both saw Misty, standing in the middle of the hallway, looking contemplative about something.

Misty turned around, looking surprised and embarrassed that they had caught her sneaking around in the hallway. She gave them both a nervous laugh, trying to mask her discomfort.

"Uh, I was looking for the, bathroom?" Even as she spoke the sentence she wasn't sure of herself.

She shifted her weight onto her other foot, not quite meeting their eyes. Drew and Ash exchanged a glance, both wondering what was going on.

"Wow, I didn't know you could get lost trying to find a restroom." Drew comments, winking at Ash when Misty wasn't looking.

Ash, confused at first, suddenly caught on to what he was doing.

"Yeah, who knew you could get lost so easily." He said, nodding his head as if he agreed.

Misty shot them each a death glare, and a specifically fierce one at that. Ash, who knew Misty well enough to know when to stop, was about to warn Drew when he spoke.

"Hm, I would've guessed a gym leader could have found something as simple as a _bathroom_." Drew said, giving her a sideways glance.

Misty opened her mouth, preparing to attack them both verbally, and if it came down to it, with her hammer. Suddenly her mouth closed, and she smiled, a wicked and evil smile.

Ash gulped, backing farther into his room.

"Let's, let's go Drew…" Ash said, pulling at his sleeve as he attempted to save him from whatever Misty had in mind.

Misty, not wanting her plan to go to waste, grabbed Drew's other sleeve. She and Ash pulled Drew's sleeves for a while, each in their respective direction. Since she was a lot stronger than Ash, she quickly managed to release Drew from his grasp, dragging him along the hallway.

Ash, who had fallen onto the floor after she had yanked him away, stood up, chasing after them.

"Hey! Where are you going?" He protested as he watched Drew hopelessly struggle against her tight grasp.

"So, I guess you're stronger than you look." Drew mutters.

Misty pretends not to notice as she opens the door to the basement, pulling in her hostage.

Ash, though suspicious, follows them in, leaving the door open slightly. He watches Misty drop Drew on the ground, in front of the girls.

"That was kinda rude, don't you think?" Drew said crossly, though no one noticed him.

May crossed her arms, eyeing him irritably.

"Why'd you bring him in here?" She asks Misty.

Misty grins, plopping down on the sofa between her and Dawn. She picks up her soda and takes a swig before answering.

"Because the dare said to bring something from Ash's room. And I did." She said, smiling victoriously.

May stares at her, looking confused and impressed at the same time. She opens her mouth to speak, but nothing comes out.

"I guess we can leave now." Ash said to Drew. They both nodded to each other, standing and preparing to leave the room when Iris jumped in front of them.

"No way! You came in here, and we were playing truth or dare. So, the girl's sleepover code strictly states that any boys who interrupt the game must also be subject to any downfalls that happen upon entering." Iris told them, flipping one side of her hair.

"Hey! I would like you to know I was dragged in here!" Drew points out, huffing quietly.

"Yeah, but were you, Ash?" Dawn asks, smirking along with the other girls as they eyed both of the boys with devious grins.

"If one comes in here by choice, the other must stay as well." Iris said, watching as Misty ran to the door, shutting it quickly, ultimately blocking the exit.

Ash, after seeing there was no way to escape, sighed, sitting down on the floor, quietly accepting his fate.

Drew rolled his eyes, but he could tell that they had no chance against four girls. He sat down next to Ash on the floor, trying hard not to glare up at the girls.

Misty, smiling, turned to the other girls. They winked at each other, and Misty pointed at Drew, indicating he would be the first target.

"Truth or dare Drew?" She asked immediately.

He blinked once, then stared up at the ceiling, trying to think. He had a bad feeling the girls were ganging up on him, so he would have to choose his answers carefully.

"Dare," He said, thinking he would be able to handle any sort of challenge from them.

"I dare you to eat a tub of ice cream," Misty, noticing Drew's relieved face, added, "from _last _year."

"What? Are you trying to give me food poisoning? And, you _have_ ice cream from last year?" Drew said, turning to look at Ash incredulously.

Ash grinned sheepishly, rubbing the back of his head.

"Well, um, maybe. Sometimes, you know, I used to like to eat the really old stuff…" He drifted off, avoiding Drew's angry gaze.

May perked up, smiling as if she was completely innocent and not conspiring against the two poor boys.

"I'm sure Misty wouldn't mind if you traded your dare for a truth." She said, keeping the innocent look on her face.

Drew raised an eyebrow, thinking hard.

_ I definitely don't want to eat that old ice cream. But, they're acting like they have something worse planned for my truth. Then again, it's either an embarrassing question or getting sick from food poisoning. The question can't be that bad…_

He reasoned, though he felt as if something was telling him not to choose truth.

He took a deep breath, then turned around, looking Misty in the eye.

"I'll trade it for a truth then."

Paul was sitting on top of his sleeping bag, waiting for Trip to come back. He had said he was just going to get a glass of water, but it seemed to be taking longer than that. He stood up, walking out of the room at a brisk pace.

Trip was examining something. It appeared to be an old recording toy, and he was turning it over in his hands, studying it carefully.

"It must belong to Ash…" He muttered, then stopped when he heard giggling.

The sounds seemed to be coming from a room down the hall. Trip, still holding the tape recorder, creeped quietly to a large door. He pressed an ear to it, and heard the following:

"So, you really choose truth Drew?" Came a feminine voice he was sure was Iris.

"Yes, that was what I said." A male voice dryly replied.

Another set of giggles were heard, but, now that Trip was closer, he realized they sounded more maniacal, and a bit more like they were about to launch some amazingly wonderful and embarrassing plan to the victim behind the door.

Trip was about to walk in to check what was happening but heard a voice which stopped him in his tracks.

"Spying? That seems classy." Paul had said, standing directly behind him.

Trip didn't even flinch, only smiling in response.

"The girls are torturing Drew and," he paused, then heard another voice, "Ash in there."

Paul crossed his arms, giving him a look.

"And you just happened to be standing right there?" He asked.

Trip was about to answer when footsteps were heard. They started to get closer, speeding up as they neared them. Both Trip and Paul froze, looking at each other nervously. Well, as nervous as they could get anyway.

"I thought someone was spying on us! Drag them in girls!" Misty said after she opened the door with a flourish.

Iris and May both hopped up, leaving Dawn to guard Ash and Drew, who stayed still and quiet. Paul and Trip though, were harder to drag than the other two.

"Why won't they get in?" Iris grumbles to May as they both push them.

Misty chuckles, snapping a finger. She nears the two boys, then leans in and whispers something in each of their ears. Their eyes both widen, and they allow themselves to be led in. The door shuts, and the boys sit next to the other boys already there.

"So, getting back to where we left off, we were just about to ask Drew a truth question, since he chickened out on the dare." May informed the boys.

Drew grumbles at this, but makes no comment. He gives Ash a sideways glance.

"How did Misty get them to come in here?" He whispers to Ash.

"I think she has blackmail material." Ash replied.

Dawn tapped her foot impatiently.

"Can we get back to playing?" She asked.

Misty nodded, her gaze settling on Drew again.

"Do you have a crush on anyone?" She asked, leaning down so she could watch his reaction.

Drew mentally screamed at himself for being so stupid as to choose truth when four nosy girls were playing.

_ I bet she can read emotions too. I guess I'll just…_

_ "_…yeah." He said finally, crossing his arms and leaning back as he tried to avoid their eyes.

"Truth or dare Drew?" May asked immediately.

He sat up, glaring at her full force.

"How is that fair? I just went!" Drew said crossly.

The girls looked at each other, smiling with mischief.

"We decided before you arrived that this was a free for all." Iris piped up.

Drew grunted, rubbing his forehead.

"Dare." He said, shooting them all an evil look.

"I dare you to kiss the person you have a crush on!" May winked, feeling very evil, but also very pleased with herself as she saw Drew's uncomfortable look.

"Uh… truth." He said, cringing slightly as he could guess what the truth would be.

"Who do you have a crush on?" May asked, as Drew predicted.

"Erm…" Drew scrambled around in his brain, trying to think fast.

_ What can I say? I can't reveal who it is… wait, I know…_

"I don't remember her name." He shrugs, looking back at them, the look of pure honesty on his face.

The girls all narrow their eyes, looking back from each other and Drew.

"What do you mean you forget?" Dawn protested, looking sad. She had gotten quite curious over who it was and not being able to know was driving her insane.

"I mean I forget," As he sees all the glares he quickly adds, "honestly."

At this point even the guys had gotten curious. Everyone looked at Drew, focusing a powerful look on him. With that many people staring you down, it was typical to feel uncomfortable. For some strange reason, Drew looked plenty comfortable. It was almost like he enjoyed irritating them all, which was probably true.

Dawn, suddenly looking happy, turned to Ash.

"Ash, truth or dare?" She asked him.

"Uh, dare." He said, surprised by her quick question but determined not to choose truth.

"I dare you to sit perfectly still while we all battle, without you." She smirks.

Ash, thinking he could easily do that, agreed. Misty walked to one side of the room, preparing to battle Dawn.

Drew was elected the referee for the match. He stood in the middle, watching Dawn stand at the other end of the room.

"Okay, this will be a one on one match. Ready, set, go!" He said, waving a napkin in the air because they didn't have any flags.

"I choose you, Starmie!" Misty said, tossing out a Pokeball.

"Then Pachirisu, you're the star this time!" Dawn said, also tossing out a Pokeball.

Misty frowned, knowing Dawn has the advantage.

"Okay, Starmie use Water Gun!" She said, her Pokemon shooting a beam of water out of it's mouth.

As soon as she had said that Ash had jumped up, yelling.

"Hey you guys! I give up, I can't just sit through a battle!" He admits, waving his arms.

Drew shrugs, waving the napkin again.

"The match is unnecessary. You don't have to continue." He said.

The girls look at each other, about to say they would rather battle when they spied a clock on the wall. It was ten o'clock; definitely time to sleep.

Iris waved the boys off with her hand, opening the door.

"We're going to be sleeping now, so bye!" She said, literally pushing them out the door.

They glance back, but the door shuts, so they all sigh, then walk back to their rooms for the night.

As Trip entered the guest room, he pulled out the tape recorder, and pressed stop. He smiled, sitting down on his sleeping bag and hiding the device before Paul entered the room.

_ I have blackmail material too._

** There it is, the third chapter! If anybody has any ideas, I would love to have them! Thank so much for reviewing, and please, keep it up!**


	4. Chapter 4

** Hello guys! I should've gotten this out before, but I was feeling lazy… Thanks for reading! Oh, wait! Also, I didn't really like the last chapter. I feel I could have done better with it, but oh well I guess.**

Pokemon: Dating Confusion

Chapter Four: Oh Snap

The girls, whilst preparing for sleep, were chatting to each other. Dawn, combing a hand through her hair, looked at May, a playful smirk on the former's lips.

"You know, the boys got off pretty easy tonight. I have a plan to make things more difficult for them." She said mischievously, flicking a stray blue strand of her hair over her shoulder.

May tilted her head, biting her lip as she thought.

"What kind of plan?" She asked, a bit wary of the younger girl's idea.

The smirk on Dawn's face quickly transformed into a grin, and a rather large one at that.

"We set them each up on a mystery date! Think about it, guys like them would get really uncomfortable on a date!" She explained to the coordinator, leaning forward on her sleeping bag, getting closer to May so they could more easily talk.

May still looked unsure as she untied her bandanna from her head, releasing her short brown locks from under it.

"Maybe it would work. But how would we go about this?" The brunet questioned.

"Er, we would… I guess I didn't think that part through…"

May sighs as she hears the response. She can't honestly say she wasn't expecting it though.

"Maybe we should trick them into signing a contract, that says they have to do it or," She pauses as she thinks, "we get to take their Pokemon for a day?" She suggests.

Iris, who had been helping Misty with the DVD player, where the girls had planned to watch a movie, came bounding over to the two coordinators.

"I like the idea, but we need to think of a better way to do this. For example, we should have the consequences be they have to give up something, permanently. We could take Ash's, Paul's, and Trip's badges, and Drew's ribbons." She concludes.

Dawn jumped, surprised in two ways. One, how the girl could run that fast. Two, how she seemingly knew so much about people she had never even met before today. But this was quickly forgotten about as she realized the boys would _have _to do whatever the contract asked. She knew the boys would never willingly give up their badges or ribbons.

Misty sighed, oblivious to their conversation as she pressed another button on the DVD player. For some reason, it wouldn't load the movie. No matter how many times she pressed 'PLAY', it wouldn't accept it. An error message would appear, rendering all of Misty's attempts useless. On a lucky occasion, it turned to the loading screen, almost as if it would play. But no, this was only a cruel trick for poor Misty. It was loading, indeed. But it was loading the VCR player, where a very old movie was currently in.

Unfortunately for our young gym leader, she did not know this. Misty, breaking into a smile of relief, turned around to face the other girls. She had been too busy with the DVD player to be paying attention to their conversation, and vice versa, because when she _was_ paying attention, she listened to their very interesting chatter.

"But how do we get them to sign it?" May asked both Dawn and Iris.

Iris spoke first, looking confident in her answer.

"We go out to eat and sit at separate tables. Then we make them 'sign the bill'." She said, indicating the bill would actually be the contract.

"But what if they don't sign it? I can't imagine they would actually pay for our food…" May said, her stomach grumbling a bit as she thought of food.

"Then we'll tell Mrs. Ketchum about our plan. Don't you think she would want her only son to have a date? I'm sure she notices he never notices girls." Dawn said, nodding to the other two.

"Can't we just ask Misty for help?" May said, starting to run out of things to protest against.

"NO!" Dawn and Iris said simultaneously, shaking their heads with venom. They both looked at each other, not noticing the fact that Misty had finished with the DVD player a few minutes ago.

Misty narrowed her eyes, wondering why they couldn't tell her.

"Seems strange to me…" She murmured under her breath in a low tone.

"Why not?" May whined.

"Because. The boys need someone to go on a date with." Iris answered, clearly indicating she wouldn't be participating in this part of the scheme.

"Wait, you aren't helping with that part?" Dawn asked, pouting as she jutted her bottom lip out.

Iris winced, unconsciously backing away. Cute stares like that made you feel guilty, and Iris didn't settle well with guilt. She sighed, rubbing a hand through her dark purple hair.

"What? I don't want to end up on a date with one of those little kids." She said, wrinkling her nose.

May nodded, agreeing.

"I definitely don't want to date any of them." She said, grimacing as she thought about how badly that could end up.

"I can't do this alone!" Dawn said, trying to convince them to help out. She suddenly face palmed.

"I have to meet Tracey tomorrow…"

May and Iris exchanged a sly look, a devious smile suddenly appearing on their faces.

"Really? What are you meeting him for?" May asked, maintaining an innocent air.

"So he can do a sketch of my Piplup." Dawn replied, unaware of the girls' motivation behind that question.

"That's it?" May asked, looking disappointed.

"Yeah, that's- wait, what do you mean by, "that's it"?" Dawn asks, her expression turning from neutral to suspicious in a matter of seconds.

"Uh, nothing." Iris said, whistling as she turned the other direction, refusing to meet Dawn's eyes.

Dawn put her hands on her hips, shooting them each a powerful glare. She tossed her head, causing her hair to shift.

Misty had been listening, and her narrowed eyes quickly turned to a laugh under her breath. She could just imagine. Dawn and Tracey. As a couple. The idea was hilarious to her, and hearing it made her want to actually see it put into action.

"Girls, I like your idea. I'm in." She said, getting their attention.

Iris's mouth dropped, looking surprised at how easily she had agreed. It closed once she realized the older girl spoke in earnest. Misty wasn't finished talking though.

"On one condition. _Everyone _here has to participate."

At Misty's sentence, the other three girls looked at each other, as if considering the idea.

"I guess."

"Sure."

"…But I have to meet Tracey at Professor Oak's lab tomorrow." Dawn points out.

Misty sighs, then beams at her, grinning from ear to ear. She doesn't say a word to Dawn, only gathering up the other girls and walking away to another corner of the room, where Misty told them her idea in whispers, leaving behind a very confused and curious Dawn. She wasn't confused for long, though, as they came back in only a minute or two, grinning like the Cheshire cat.

"Well Dawn, I said I would only do it if everyone joined in the fun of dating one of the boys. So, if you made this a date with Tracey…" Misty trails off, leaving the rest for Dawn to figure out.

The blush on the blue-haired girl's face is huge, and a bright, tomato red blush too. Dawn clenched her fists, looking up at them.

"It's not a date! And why would I go out on a date with him?!" She asks angrily.

"Because, we girls will go out with someone too." Misty said soothingly, knowing that she would be able to win this argument.

"But, but he doesn't even think it's a date!" Dawn said, her blush only increasing as she tried to prevent it from doing so.

"Do men _ever _think it's date?" Iris muttered sarcastically under her breath to May, who nodded solemnly in agreement.

"Exactly. Men never think of it as a date. Even if it is one. So what's the difference? It only matters that _you_ think it's adate." Misty concluded.

"But…" Dawn ran out of things to complain about, so she shut her mouth, though she looked very unhappy about this arrangement. She opened it again soon after, and glanced up at Misty.

"Okay." She said, barely above a whisper.

The other three girls beamed, high-fiving each other.

"Yes! Now, to see who everyone else has to date." Misty hopped up, rushing into a trunk in the corner, which she had seen earlier. As she guessed, there were a few stray pieces of paper in there. She took out a pen from her pocket, and wrote something down.

"Choose one. Whichever one you choose is the person you date." She said as she crumpled up the sheets of paper and tossed them on the floor.

May looked worried, wondering who she would end up with. She gingerly reached for the one closest to her, grasping it with one hand. She brought it up to herself, and carefully opened it up, careful not to rip it. She read the name, then looked disgusted.

"I got Trip…" The fact she had to date the younger boy was making her feel a bit nauseous.

"Oh…" The girls all said sympathetically, shaking their heads.

Iris looked sorry for May, so she tried to be extra cautious in choosing her own. She took the one that was closest to the middle of the room, hoping it wasn't bad. She opened it, and wasn't sure how to react.

"I got Drew."

No one said anything. There was a strange silence before May started laughing.

"Good luck! That's going to be an interesting date." She chuckled to herself, shaking her head.

As she realized she was the only one laughing, she looked up, wondering why no one else was. She realized they were too busy looking at Misty, who seemed to have just picked up her own and was looking at it with horror.

"What's wrong? Who did you get Misty?" May asked, crawling over the mounds of pillows and blankets to reach the group. As she peeked over her shoulder she realized why they were so quiet.

"You got Brock?!" May exclaimed, looking shocked. Forget having to date Trip; dating Brock was the most horrible thing that could befall a girl.

"I'm so sorry Misty."

Misty shook her head, a look of resolution on her face.

"It's bad, but I can live with it." She said bravely, though looking as if she would rather face a group of Beedrill than date Brock. She sighs, climbing into her sleeping bag as the movie finally got past the commercials. As she closed her eyes, waiting for sleep, she thought about all the adorable Water Pokemon, back at the gym. They were probably snug and warm, relaxed, without a care in the-

"Misty, this is the VCR playing…"

"Gah!"

The next morning was peaceful, and very bright. The sun rose, showing off its brilliant beams. Sadly, it happened to do this at six in the morning, and woke everyone in the basement up.

"Why did the sun have to rise this early again?" Misty grumbled as she helped the other girls clean the room.

May was glad Max wasn't there; he would have come up with a scientific explanation for it. She shrugged, stifling a yawn.

"Let's just hurry. Then we can get this over with." Dawn said, feeling grouchier than usual.

"Hey, wait a minute. These dates, they're going to be our first date, aren't they?" May said suddenly.

Everyone looked at each other, a look of complete annoyance on their faces.

"My first date is Brock!"

"I have to date a guy with green hair."

"I'm dating someone younger than me."

"I'm going out on a date that you guys forced me to that is only real from one side!" Dawn said in a rush, stomping out of the room in a huff.

The other girls simultaneously glared at each other, mumbling things under their breath as they followed the cross-looking girl. As they entered the kitchen, they soon forgot about their misfortunes as they smelled a delicious aroma wafting from one end of the room.

As they breathed in the delightful smell, Mrs. Ketchum turned around from the stove, where she was cooking pan cakes.

"I didn't know you girls were up already! I just got up so I could get some breakfast before Ash ate all the pancake mix." The woman explained.

They nodded, dreamily thinking about the food.

"I can make you girls some right away!" Mrs. Ketchum said, bustling around the stove in a cooking frenzy, pouring batter into another pan in a hurry.

"Oh, it's really okay Mrs. Ketchum. You go ahead and eat, we can wait." Misty said, noticing a plate already set at the table.

"No no no! I'm fine, you girls sit down and relax." The older woman said firmly.

They sat down, not wanting to disobey. As they watched her cook, their thoughts drifted off to their dates that day.

_ What should I wear?_

Dawn wondered.

_ How am I going to get Trip to go out with me?_

May thought.

_ I really wish I didn't have to date Green-Hair…_

Iris sighed.

_ I have to date Brock. I. Have. To. Date. Brock. I HAVE TO DATE BROCK!_

** Sorry this one is shorter than the others. My muse dropped. Like a rock. Anyway, keep reviewing and I'll keep writing! I am happy that people are enjoying this!**


	5. Chapter 5

** Guys, I am so sorry. I promised myself not to randomly disappear, but I did. To be fair, I caught the flu. Though, it seems like a weak excuse… Anyway, here is the chapter! I hope you enjoy! **

Pokemon: Dating Confusion

Chapter Five: Just Try It

Trip was exhausted that morning. He usually awoke quite early, most days at least seven in the morning. But, waking up at six in the morning, that was something completely different. Now, if he had gotten a full night of rest, it wouldn't have been that big of a deal. Unfortunately, he had not gotten one. Paul. Paul was why he had not gotten any sleep. It was his snoring that kept the young trainer awake all through the night. One would not think Paul snored so much, or so loudly, but he did. Indeed he did. Trip had recorded some of it for proof, to show to the others if it became necessary. And on top of getting no sleep, Paul just had to wake up at six in the morning. He just had to release his Pokemon for some early morning training too. They just had to disrupt his sleep. Well, now Trip just had to go to war with this despicable person. Disturbing someone's sleep should be a criminal offense.

Trip had been clutching a rolled up magazine, preparing to give Paul a nice smack on the back of the head. But, fate decided to be kind to Paul. As Trip prepared to make the swing, the waft of pancakes floated into the room, eventually reaching Trip's nose. He dropped the magazine, turning tail and walking, in as fast a way without being able to call it running, down the hallway, coming to a screeching halt right outside the kitchen. Slowly opening a door, he was greeted with the sight, and of course smell, of pancakes.

He noticed the girls were already awake, smiling and chatting happily to each other as they munched on their syrup-covered deliciousness. It was lucky Mrs. Ketchum saw him, because if it had only been the girls, he might have stood there for a year without being noticed, because pancakes happen to be very distracting.

"Why good morning Trip! You're up early too?" She said, turning around and giving him a warm smile.

"Eh, I guess you could say that." Trip shrugs, heading toward the table and taking a seat across from the girls. He leans back in his chair, avoiding any eye contact.

"Do you want some pancakes too?" Mrs. Ketchum asked him sweetly.

"Pancakes?" He could feel his nose wrinkle, and he opened his mouth to say no when Misty piped up.

"I think that every good Pokemon trainer needs to eat a healthy breakfast!" Trip rolled his eyes.

_ So, she's turned into a pancake mix commercial?_

Trip thought sarcastically before replying.

"Since when are pancakes healthy?" He said, doing his best to stay calm after his sleepless night.

Misty wasn't phased at all, merely grinning cheekily in response.

"Mrs. Ketchum only makes pancakes with whole wheat and all natural ingredients! Also, there's eight grams of fiber in a serving."

At this point Trip was firmly convinced that this young girl was really a salesperson in disguise. He could easily imagine her in a business suit, smiling at a camera, probably holding some kind of weird product no one really wanted to buy but commercials tricked you into buying them anyway.

He actually had proof of this; once when he was much younger he had called one of those '1-800' numbers and ended up with a cheap, plastic Rhydon and his monthly allowance gone.

He was busy reminiscing when Misty spoke again.

"See Mrs. Ketchum? He's thinking of how delicious the pancakes are!" That girl. She was very annoying.

"Actually, I may just get some cereal." Trip said, moving toward the cabinets. He honestly **did **want some pancakes, but he wasn't going to tell them that. Though at this rate, that Misty would probably make him eat some…

"Oh come on Trip! Just eat pancakes like a normal person!" May said, rolling her eyes. She thought he must be crazy to not want pancakes. Did he appreciate food at all? May wasn't quite sure.

"Yeah, these are really good!" Dawn said, smiling kindly at May, helping her out.

May smiled back, but a wave of confusion washed over her as Dawn's grin turned into a devious smirk.

_ What's that look about? I didn't do anything- oh… Not now! Do I have to ask him now? I want to relax and eat my pancakes._

May whined in her head, then decided there was no purpose of fighting it. She would have to do it anyway, so why not now?

_ Because I don't want to._

May's brain answered back. She sighed, then forced a smile and faced Trip.

"Er, want to go get some breakfast somewhere else, then? I don't think there's any cereal here…" She honestly didn't know if they had cereal or not, but for her sake she hoped not. Or maybe she hoped they did. At least then she wouldn't be able to go out with him.

Trip paused noticeably, and shifted his weight slightly onto another foot. He remained silent as he considered the offer.

_ Did she just ask me out? Don't know whether to be flattered or throw up… then again, accepting the offer would let me leave the house, away from the red head…_

After a few more moments of thought Trip gave her a curt nod, then strode across the floor to the other side of the kitchen, where the door was. He opened the door and stepped outside into the brisk morning air, then waited, still holding the door open.

"I don't have all day you know." He said, a tad bit impatiently.

May glanced up at him, then gazed back down at the plate of uneaten pancakes. She stared at them hungrily, and for a moment she wished she could just sit there and eat them, happily ignoring the rest of the world. Yep, just her and the mound of syrupy goodness, with a delicious pat of butter and some wonderful strawberries on top. May almost got lost in her reverie, right before Misty gave her a hard nudge in the ribs. It quickly reminded her why she would rather date Trip than face the wrath of any of the other girls. So, with a heavy sigh she stood up, getting farther away from the pancakes. She managed to do it successfully, meaning she didn't immediately rush back and devour them. The brunette reached Trip shortly after, and they walked out the door together.

As soon as they were both out of hearing range, Iris jumped into the air, fists pumped.

"Yes! One girl down, three to go!" She cheered, her Axew being disrupted from his peaceful rest. He shot her an annoyed glare before shaking his head, rolling over and closing his eyes to rest.

"What?" Mrs. Ketchum looked very confused as she turned around to look at them. She seemed to have no idea what they were talking about.

"Uh, well, er, we kind of made a bet. You see, last night we decided to tease the boys, so we made a plan to-" Dawn was interrupted by Misty, who clapped a hand over the younger girl's mouth.

"To take them out to lunch! You know boys, never feeding themselves properly. Ash always needed Brock or one of us to help him while he was traveling, right?" The gym leader said, turning to give the others what looked like a threatening gaze, telling them to agree. Until it hit Misty.

_ Wait, what am I doing?! If I let Mrs. Ketchum know, then maybe I won't have to date Brock!_

She though excitedly.

Unfortunately, it was a bit late for that. The woman had already believed that excuse. And the fact that both Dawn and Iris were nodding with extreme vigor probably helped that fact. Misty growled to herself, but otherwise remained silent.

Dawn scooted away from her, fearing that the mallet would come out soon if Misty got any angrier. She played with her food, shuffling a piece of pancake to one side of the plate. She nibbled another piece, then leaned her head on her arm, looking deep in thought.

_ Hm, I wonder if Tracey will think it's a date. I hope not. But then again, I don't seem to be very lucky with these things… I wonder when exactly I'm supposed to meet him? I guess I could go now, since May already left for her 'date'._

Dawn pushed the plate away and stood up, brushing her sticky hands against a napkin in a futile attempt to clean them. She looked up at the other girls, who seemed to be able to tell what she was thinking. She took a deep breath, then scurried away, yanking open the door and rushing out before Mrs. Ketchum could offer her seconds.

She walked down the small road to the professor's house, where she was supposed to meet Tracey. The bluenette ran a hand through her long hair, briefly wondering if she should have styled it up. She then shook her head with such power she later was surprised it hadn't fallen off on the spot. As she neared the house, she happened to look to her right, and was very surprised to see May and Trip still walking around, not having reached their restaurant yet. They didn't notice her, so she continued to walk away, though a bit curious as to why they hadn't arrived yet. She didn't know that the road was closed off, and the only way to get past was with a Flying Pokemon. So as Dawn knocked on the door of the professor's house, May and Trip were heading back to borrow a Pokemon.

"I can't believe that you didn't bring a Pokemon that can fly." Trip informed May with a tone of shame, clearly disappointed in the older girl's abilities.

May felt her face heat up, with anger, not a blush, thankfully.

"What about you? Why don't you have a Flying Pokemon?" She countered crossly, huffing as she walked ahead of him.

"I decided they weren't necessary so I didn't bring any." He replied calmly and coolly, ignoring her irritation.

"Well, just, humph!" May, who couldn't think of a good enough comeback, stomped farther away from the blonde, muttering unsavory things under her breath. She was feeling very cross, so she decided that if he said one more rude thing she would explode. Therefore, in order not to explode, she ran far ahead, reaching the house in a matter of minutes.

She rang the doorbell, then remembered it was open. She burst through the door, and was surprised to see that everyone was up. She didn't let her surprise stop her from her mission though; she ran up to Ash and practically shouted in his ear,

"CAN I BORROW A FLYING POKEMON?" She had no idea that her voice could yell that loudly before that moment.

Ash, only momentarily deaf, winced, then took a Pokeball out of his belt. He handed it to her, blinking a few times.

"S-sure," He started carefully, not knowing why May had gone berserk, "but why?" He asked as she accepted it.

"Oh, I just needed a Flying Pokemon. The roads were being closed for construction." She told him cheerfully before heading back outside to where Trip was waiting.

He, as soon as he saw she was holding a Pokeball, turned around wordlessly, heading back toward the road where they needed to fly over.

Meanwhile, inside the Ketchum house, everyone was still curious why she had barged in like that.

"I'm surprised that girl can yell with such power." That comment came from Drew, who was acting very picky with his plate of pancakes.

Ash shrugged, along with his Pikachu, who had managed to sneak past Mr. Mime to the fridge and was now happily slurping up some ketchup.

"Maybe she was in a mood." He suggested, and a lot of the others nodded, of those who knew May, that is.

Misty stood up and rushed out of the door as if she had suddenly forgotten something. As the group wondered what had happened with her sudden disappearance, Misty was already halfway to the professor's house. As she plodded along the road, she caught sight of another figure. It looked like Dawn for some reason. Why would Dawn be- Misty facepalmed as she realized the answer. Tracey. Tracey was staying with the professor, so that was why Dawn was there. At least another girl would be there, almost for moral support, hopefully. They both waited, since Dawn had knocked before. Thankfully, the door quickly opened, and Gary was behind it.

"Hey Misty." Gary said with a smile. "And Dawn." He added, though his gaze was focused on Misty.

Misty wasn't paying attention, and she merely swept past him, walking into the house and glancing around.

"So, do you know where Brock is?" She asked, getting straight to the point.

Gary shrugged, then pointed to a door. Misty nodded her thanks, then reached over and opened it by turning the knob. As it creaked open Misty saw a kitchen, and all the boys were seated at the table, chatting to each other.

Misty paused for a moment, contemplating what style would be the best way to approach Brock. She settled on her normal way she would approach him. So with that figured out, she marched straight across the red tiled floor and stopped straight in front of Brock, placing her hands on her hips.

"We're going out to brunch." It was not an offer. It was a command. She didn't even have the grace to wait for an answer; she immediately grabbed his ear and dragged him out of the kitchen.

Dawn watched the peculiar scene, and couldn't help giggling. It was funny to watch Misty, a girl younger than the Pokemon breeder, pull him across the floor so easily.

Tracey, previously sucked into sketching a Butterfree outside the window, looked up after hearing Dawn laugh.

"Hi Dawn! Is your Piplup ready to sketch?" He asked curiously, putting the pencil behind his ear and holding the sketchbook under his arm.

"Huh? Oh, right." Dawn nodded, then followed Tracey out of the house, right behind Misty and Brock, who the red head had decided to have mercy on and let him walk himself.

As they continued on, Misty, Dawn, and even Brock were having their own feelings of dread, not knowing what would have happened by the end of the day.

** I know it's shorter than usual, but it's better than nothing, right? Hehe, anyway, I really hope you enjoyed! Thanks to everyone who reviewed, followed/favorited, and of course just read! I always accept reviews, just to let you know… oh, one more thing. I think this story will have around ten chapters if everything goes as planned. But that's just the plan. Anyway, R and R please!**


	6. Chapter 6

** The newest chapter! I made it as fast as I could, since I was inspired by a Pokemon marathon a few days back. I love how everyone is being really nice with reviewing! Thank you wonderful people so much!**

Pokemon: Dating Confusion

Chapter Six: Introducing TR

May hummed lightly to herself, almost skipping as they neared their destination. They could see the road ahead, so they knew they were close. May fingered the Pokeball Ash had given her, suddenly remembering she hadn't bothered to ask which one she had received. She shrugged to herself, obviously not thinking the fact important. The brunette smiled quietly to herself as she stopped, only a foot away from the side of the road.

"So, are you ready for breakfast?" She asked Trip cheerfully, tossing the Pokeball and releasing a Pokemon.

Trip was about to answer, but he stopped when the creature took shape. It had large wings on its back, almost horn-like things on its head and huge claws. Trip gazed up at it calmly, tilting his head as he looked it over.

"So, he gave you his Charizard." He commented, pulling out a camera and snapping a quick photo.

May nodded, rubbing her hands together happily.

"This is going to be so awesome! Let's go Charizard!" She said, climbing onto his back easily.

Charizard shot her a warning look, but at this point the was well-mannered enough to only fry Ash with Flamethrower. He allowed her to climb onto his back, but Trip was another story.

Charizard flared his nostrils threateningly at the boy, daring him to climb onto his back. He didn't like the kid's attitude, and wasn't about to allow him the pleasure of getting to ride him.

Before either May or Trip could protest, he lifted into the air, leaving Trip still on the ground. May gasped, but couldn't suppress a small chuckle which wormed it's way out of her throat.

"Is it weird that I think you're awesome Charizard?" She asked with a laugh as the dragon roared at Trip, almost mockingly.

Trip shot her an unamused look, then tapped his foot with impatience.

"Just bring down that thing so we can hurry up and get something to eat." He grumbled, looking cross.

She replied by sticking out her tongue playfully, then sighed and rubbed Charizard on the back of the neck.

"I don't think Charizard wants to let you on." May informed him in a teasing tone, winking at him.

Trip, was starting to debate if she was only joking or if she was serious. It was a high possibility that she would take off without him. Judging from what he had seen of her so far, it wasn't hard to peg her as that type of girl when it came to food.

"You know… I bet I could get Charizard to take me to the food place. I bet he only lets on nice people." She said, smiling at Trip, though it seemed more like a smirk.

Charizard, deciding he had been too courteous to this girl for too long, shrugged her off of his back. She landed in a heap on the ground, not hurt from the short fall, but a bit irritated.

"What was that for?!" She demanded, shaking her fist at the dragon.

Charizard answered by puffing out some smoke at the young girl, curving its' lips up into a small smirk.

"Let me back up!" May yelled, jumping up and down in an attempt to hop back onto the dragon. She, after failing numerous times (and exhausting herself), gave up, collapsing to the ground.

"Really?" She whined, looking up at him.

"You were actually trying to mount a flying Charizard?" Trip's tone revealed a hint of amusement as he stood beside her.

"I wasn't talking to you!" She snapped, already feeling tired after just what had happened so far that day.

"Hm. And who were you talking to then?" He replied, glancing up at the sky.

"To Charizar-" May suddenly stopped mid-sentence, letting out a surprised cry.

"Where'd he go?!" She exclaimed, frantically bouncing up from the ground and beginning to panic.

As she looked up at where the dragon had been, she saw, with a hint of despair, the form of Charizard, flying away without them. It was too late to return him, though, seeing as he was already too high for his Pokeball to reach.

"Great. Now what do we do?" May moaned, going through her Pokemon she had brought with her mentally in her head.

_ Let's see, maybe I could use- no, he can't fly. Or I could- no, Venusaur can't fly either. Shoot, I don't have anything?!_

May sighed, glancing over the road that led back to the house.

"I guess we could always borrow someone else's Flying Pokemon." She suggested, beginning the short walk back to the house.

"Aren't you forgetting something?" Trip asked her, raising an eyebrow as he followed the girl with his arms crossed.

"What do you mean?" The brunette replied, already in a better mood as she hoped they would be in time to get breakfast at the restaurant before she went on a crazy rampage from not having enough food.

"You know you just let Charizard roam the city alone, right?"

After letting the comment sink in, she gasped, whirling around to face him as her eyes bulged.

"WHAT?!"

"It's your own fault."

"You were supposed to be helping me!"

"Charizard didn't want to let me on, remember?"

"Grr, shut up and let's go find that dragon." May said crossly, stomping off toward the house.

"Why are you heading back here? You know Ash is going to go crazy when he finds out **you **lost his Pokemon." Trip said, putting extra emphasis on the you part as they neared the house.

May paused, hesitating before answering.

"You might be right," she began slowly, "but I have to get _someone _to help!" She finished decidedly, stepping on to the porch and creaking the door open.

She thought she saw a figure in the bushes when she pushed the door open, but it disappeared after taking a closer look. But once she stepped inside the house, with Trip right beside her, she didn't realize that more than one figure was lurking in the bushes outside.

"Did you hear them talking earlier about that Charizard? We could show that to the boss! Don't you remember how powerful it was, James?" The woman of the grouped asked, her green eyes flashing.

"Yes I do, Jessie, the distinct things I remember having to do with being on the receiving end of that power." James replied, sighing.

He knew easily what came next. They captured the Pokemon, the twerp and his Pikachu shocked them into the sky, and they redid the cycle over, and over, and, well, you get the idea.

Jessie, being used to James' hesitancy with these things, brushed it off, knowing James would listen to her idea anyway.

"Who cares? That was then and this is now. Come on, we can beat the kid easily."

"Maybe the kid, but what about his Pikachu?" James protested feebly, still wanting to go a day or two without 'blasting off again'.

"Quit being such a downer! And with all of the twerps and twerpettes here, we can take all of their Pokemon at once!" Jessie said with a smile, already thinking about the praise they would get from the boss.

"Or we'll get hit from all sides." James muttered under his breath, wincing as he thought about how painful it would be to be hit by so many attacks at once.

"I said to quit being such a downer!" She said, giving him an icy look.

"S-sure thing, Jessie." James quickly complied, knowing that an angry Jessie hurt a lot more than a Pikachu's Thunderbolt.

"Say, where did Meowth go?" He asked, a trickle of curiosity showing up on his face.

"Oh, I sent him off into town. The first twerpette is having lunch with, um, I think he was named Brock." She replied, waving a hand to indicate it didn't really matter to her.

James eyes widened, then he snickered under his breath.

"I guess our little twerps have all grown up." He said, wiping a fake tear from his eye.

Jessie rolled her eyes before thinking for a minute.

"I wonder if this means they're dating? Oh, romance can be so beautiful!" She said, clasping her hands together and smiling dreamily to herself.

"How would you know? It's not like you've ever had a boyfriend."

After a loud slapping sound, the seemingly innocent comment made by James had set Jessie's eyes on fire.

"Oh, I see. I'm not pretty enough to have a boyfriend, right?" She almost hissed, her face darkening as she leaned in and faced him.

He gulped, starting to back away.

"N-now, J-jessie, maybe we should go check on how Meowth is doing…" He said, glancing back and forth nervously, looking for an exit.

"You're right. So go check on how he's doing!" She said, kicking him into the sky with her boot, directing him toward the city.

He was at the falling stage now, heading toward a suspicous looking man in a trenchcoat.

"Hm, now let's see, I think I gotta go to da' second street before I-" The unsuspecting 'person' said, taking a lucky step to the left as he stared at the map in his paws.

"Aah!" Came a shout, before a streak of white flew past him, landing right beside the man.

Meowth didn't look up from his map as he heard something start to stand up.

"Jessie again, huh?"

"…you know us too well."

Misty, currently sitting in a chair across from Brock at an outdoor table, whipped her head around quickly and saw a man who looked like he fell out of the sky.

"Brock, I think some guy forgot his parachute in the plane or something when he was skydiving." She said, wondering why the man was being dragged along by a shorter person in a trenchcoat.

Tracey, who had set up an art easel beside the platform of the restaurant they were in, was sketching Dawn and her Piplup when he answered.

"It was probably just a stunt or something. Or maybe it was one of those stupid TV shows where they make you do crazy things for money." The artist suggested.

Brock frowned, sipping his drink and simulteneously shaking his head.

"No, that didn't look like a stunt." He decided, leaning back in his chair.

"Well, whatever it was, he looks okay." Dawn said with relief, staying still as she noticed the man was on his feet, though he had a red mark on his cheek that looked like he'd been slapped.

They sat, or in Tracey and Dawn's case, stood in silence for a few moments. Until a waitress arrived to deliver the check, to which Brock immediately jumped up and grabbed her hands.

"Do you believe in love at first sight?"

Misty sat up in her chair, getting really sick of Brock's cheesy lines. She was tempted to slap him right then and there, but she decided that doing so might create a less than favorable circumstance.

The waitress soon turned around and looked at Misty, but she seemed confused.

"Weren't you here with another boy yesterday?" She asked, tilting her head at the gym leader.

Misty returned the confused look until it hit her; she had gone with Gary.

_ Great, so now she probably thinks I'm cheating on my boyfriend or something. She couldn't be more wrong. Gary and Brock, __**neither **__of them are my boyfriend._

She thought crossly to herself, then had an idea.

"No, Brock here is my brother." She said, hoping that explanantion would work.

"Oh, I see. Anyway, here's the check." A bright smile appeared on the waitress's face as she walked away, her high heels clicking on the tile floor.

"Um, what just happened?" Asked a very confused Brock, who had stayed silent during the girls' exchange.

"What are you guys talking about?" Iris asked, who was walking up to them with Drew, who didn't look like he wanted to be there at all.

"Nothing much." Misty replied with a shrug, not wanting to explain the whole ordeal that had just happened.

"Okay." Iris shrugged, sliding into a seat beside Misty. She propped up her chin and looked at the older girl.

Misty looked back at her, then leaned in and whispered something in her ear.

"How did you get Drew to come? May says he's really stubborn." She said quietly so only the two of them could hear.

"Oh, I just told him that if he didn't I would tell everyone that he was too chicken to eat breakfast at a cheap restaurant."

Misty frowned at her explanation.

"From what May has told me, I don't think that would do it…"

"Okay, fine. I said I would pay for breakfast." Iris admitted with a sigh.

"That sounds more like Drew, though I think he was using it as an excuse to tease you about it, most likely." Misty decided, nodding.

"Yeah, but, hey, I think we all completed our dares!" Iris suddenly said, beaming.

"What about May?"

"Oh, I forgot about her…"

Misty facepalmed, then looked up at Brock. He seemed to be distracted, as he was looking at every waitress in the restaurant.

Drew was watching them with a bored look on his face, leaning against a wall right beside them. Out of the corner of his eye he watched Tracey sketch Dawn, and had to admit he was impressed with his talent.

Meanwhile, with Jessie. She had met up with the boys behind a factory, where she seemed to have forgotten about what James had said earlier.

"Okay! Now, Meowth, what did you see?" She asked curiously.

"Well, not much if ya want da' truth. It got so borin' I walked here ahead a' time." The Pokemon answered.

"Hm, okay then. I say we launch our attack at one hour from now!" Jessie said, looking from one boy to the other.

"Alright." James and Meowth said simultaneously, then both sighed, shaking their heads.

They mentally prepared to blast off in one hour and fifteen minutes from now.

** There you go! I hope you liked this chapter, and if you did, reviews never hurt anyone ****J****. Oh, before I forget, here's some cookies to everyone who's reading this story. Chocolate chip! (I'm actually having chocolate chip cookies tonight.)**


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